Experience the Caribbean like never before


Every trip is Custom and Private

Just select your trip, we take care of rest

Top Trips

Experience The Best Of The USVI With Our Featured Trips.

*We do not offer BVI trips at this time

Day Trips

Experience the beauty of the US Virgin Islands on a Private Charter.

Book BlackSheep Charters for an ALL-INCLUSIVE full day experience like no other.

Airport Drop Off/Pickup

Start or end your vacation in the best way possible! We offer direct drop off or pickup half a block from the airport.

Extended Day Trip

Explore all of what the USVI has to offer with our extended Sunset Trips

The #1 Owner Operated Charter Company

With 5+ Years of Experience you should expect nothing but the best from us!

Private Vessel

We Do Not Sell Seats, so the Entire Boat is Yours!

All Inclusive Trips

We have everything you would need for your day, you only need to bring a towel and sunscreen.

Fully Customizable

Our Captain will give recommendations based on what you would like to do, but you decide the itinerary!






Years of Experience


Experience the excellence seamless adventures, outstanding customer care, and rave reviews. Join us for unforgettable memories!

My husband and I booked a Full Day with Connor and it was absolutely phenomenal! We told him what we were looking for, and he made it happen! I wanted to see great coral – he made it happen. We wanted to se sea turtles – he took us to the perfect spot. Not to mention, he had these water scooters that seriously were a game changer for snorkeling! Their boat is in amazing condition, kept very clean and well taken care of. As well as all the gear they provide!
10/10 recommendation booking with Connor!

Meghan C.

I have been on several trips with Connor, from a comfortable family only day to several raucous party days.
Extremely professional with an intimate knowledge of where to be and when. This is the real deal and absolutely worth every penny!!

Ron P.

Had a fantastic day aboard the Blacksheep!! Captain Connor and of course Kali the dog, took such great care of us. 4 of us went out for the day on a fabulous adventure. Great snorkeling around Maho and Waterlemon Cay. Such beautiful areas all to yourself aboard the BlackSheep. Great lunch, fruits, veggies ,drinks etc. Perfect day!!! Has all the snorkeling equipment you need and SUPs ,floaties etc. You can stay as long or short at a place you want. Connor is always there to take you. Full sail up return back to Red Hook. Highly recommend!!!!

Cynthia G.

Kick off your Island Adventures by beginning the journey with us.

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